Heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I)in which X, R1, R2, R3 and n have the definitions given above,to the use thereof as acaricides and/or insecticides for control of animal pests and to processes and intermediates for preparation thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the National Stage entry of InternationalApplication No. PCT/EP2018/050102, filed 03 Jan. 2018, which claimspriority to European Patent Application No. 17150791.6, filed 10 Jan.2017.

BACKGROUND

Field

The present invention relates to heterocycle derivatives of the formula(I), to the use thereof as acaricides and/or insecticides for control ofanimal pests, particularly of arthropods and especially of insects andarachnids and to processes and intermediates for preparation thereof.

Description of Related Art

Heterocycle derivatives with insecticidal properties are alreadydescribed in the literature, for example in WO 2010/125985, WO2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/180193, WO2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO2016/124563, WO 2016/124557, WO 2015/121136, WO 2015/133603, WO2015/198859, WO 2015/002211, WO 2015/071180, WO 2015/091945, WO2016/005263, WO 2016/039441, WO 2015/198817, WO 2016/041819, WO2016/039441, WO 2016/039444, WO 2016/026848, WO 2016/023954, WO2016/020286, WO 2016/046071, WO 2016/058928, WO 2016/059145, WO2016/071214, WO 2016/091731, WO 2016/096584, WO 2016/107742, WO2016/107831, WO 2016/113155, WO 2016/116338, WO 2016/121997, WO2016/125621, WO 2016/125622, WO 2016/129684, WO 2016/142326, WO2016/142327, WO 2016/169882 and WO 2016/169886.

Modern crop protection compositions have to meet many demands, forexample in relation to extent, persistence and spectrum of their actionand possible use. Questions of toxicity, sparing of beneficial speciesand pollinators, environmental properties, application rates,combinability with other active ingredients or formulation auxiliariesplay a role, as does the question of the complexity involved in thesynthesis of an active ingredient, and resistances can also occur, tomention just a few parameters. For all these reasons alone, the searchfor novel crop protection compositions cannot be considered complete,and there is a constant need for novel compounds having improvedproperties compared to the known compounds, at least in relation toindividual aspects.

SUMMARY

It was an object of the present invention to provide compounds whichbroaden the spectrum of the pesticides in various aspects and/or improvethe activity thereof.

Novel heterocycle derivatives have now been found, these havingadvantages over the compounds already known, examples of which includebetter biological or environmental properties, a wider range ofapplication methods, better insecticidal or acaricidal action, and goodcompatibility with crop plants. The heterocycle derivatives can be usedin combination with further agents for improving efficacy, especiallyagainst insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I)

in which (configuration 1)

-   -   R¹ is (C₁-C₆)alkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₂-C₆)alkenyl,        (C₂-C₆)haloalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl or        (C₃-C₈)cycloalkyl,    -   R² is hydrogen, (C₁-C₆)alkyl, (C_(l)-C₆)haloalkyl,        (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,        (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,        (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,        (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,        (C₂-C₆)haloalkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,        (C₂-C₆)cyanoalkynyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,        (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl,        cyano(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,        (C₁-C₆)haloalkylthio-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,        (C₁-C₆)haloalkylsulfinyl-(C₁-C₆)alkyl,        (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl,        (C₁-C₆)haloalkyl-sulfonyl-(C₁-C₆)alkyl,        (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl,        (C₁-C₆)haloalkylcarbonyl-(C₁-C₆)alkyl,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl or        (C₁-C₆)haloalkoxycarbonyl-(C₁-C₆)alkyl,    -   R³ is optionally singly or multiply, identically or differently        substituted (C₃-C₈)cycloalkyl, where possible substituents in        each case are: (C₃-C₈)cycloalkyl, (C₁-C₆)alkyl,        (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,        aminocarbonyl, aminothiocarbonyl, halogen or cyano,    -   X is a heteroaromatic 9-membered or 12-membered fused bicyclic        or tricyclic ring system from the group of Q1 to Q18

-   -   R⁴ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,        (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,        (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,        (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,        (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl or        (C₃-C₈)cycloalkyl,    -   R⁵, R⁶ are independently hydrogen, cyano, halogen, (C₁-C₆)alkyl,        (C₁-C₆)haloalkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl,        (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,        (C₁-C₆)haloalkyl-(C₃-C₈)cycloalkyl, cyano-(C₃-C₈)cycloalkyl,        halo-(C₃-C₈)cycloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkoxyimino, (C₁-C₆)haloalkoxyimino (C₁-C₆)alkylthio,        (C₁-C₆)haloalkylthio, (C_(l)-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl,        (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkylsulfonyloxy,        (C₁-C₆)haloalkylsulfonyloxy, (C₁-C₆)alkylcarbonyl,        (C₁-C₆)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkyl-aminocarbonyl,        (C₁-C₆)alkylsulfonylamino, (C₁-C₆)alkylamino,        di-(C₁-C₆)alkylamino, aminosulfonyl, (C₁-C₆)alkylaminosulfonyl        or di-(C₁-C₆)alkylaminosulfonyl,    -   n is 0, 1 or 2.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

It has additionally been found that the compounds of the formula (I)have very good efficacy as pesticides, preferably as insecticides and/oracaricides, additionally generally have very good plant compatibility,in particular with respect to crop plants.

The compounds according to the invention are defined in general terms bythe formula (I). Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated hereinafter:

Configuration 2

-   -   R¹ is preferably (C₁-C₄)alkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,        (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl or        (C₃-C₆)cycloalkyl,    -   R² is preferably hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,        (C₁-C₈)cyanoalkyl, (C₁-C₈)hydroxyalkyl,        (C₁-C₈)alkoxy-(C₁-C₈)alkyl, (C₁-C₈)haloalkoxy-(C₁-C₈)alkyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        cyano(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,        (C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl or        (C₁-C₄)haloalkylsulfonyl-(C₁-C₄)alkyl,    -   R³ is preferably optionally singly or multiply, identically or        differently substituted (C₃-C₆)cycloalkyl, where possible        substituents in each case are: (C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,        (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        aminocarbonyl, aminothiocarbonyl, halogen or cyano,    -   X is preferably a heteroaromatic 9-membered or 12-membered fused        bicyclic or tricyclic ring system from the group of Q1 to Q18,    -   R⁴ is preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl or        (C₃-C₆)cycloalkyl,    -   R⁵, R⁶ are preferably independently hydrogen, cyano, halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,        (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,        (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,        (C₁-C₄)haloalkyl-(C₃-C₆)cycloalkyl, cyano-(C₃-C₆)cycloalkyl,        halo-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)alkoxyimino, (C₁-C₄)haloalkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,        (C₁-C₄)haloalkylsulfonyloxy, (C₁-C₄)alkylcarbonyl or        (C₁-C₄)haloalkylcarbonyl,    -   n is preferably 0, 1 or 2.

Configuration 3

-   -   R¹ is more preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl or (C₃-C₆)cycloalkyl,    -   R² is more preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₃-C₆)cycloalkyl or halo(C₃-C₆)cycloalkyl,    -   R³ is more preferably optionally singly or multiply, identically        or differently substituted (C₃-C₆)cycloalkyl, where possible        substituents in each case are: (C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,        (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, halogen or        cyano,    -   X is more preferably a heteroaromatic 9-membered or 12-membered        bicyclic or tricyclic ring system from the group of Q1, Q2, Q3,        Q4, Q5, Q6, Q10, Q11, Q12, Q13, Q14, Q15, Q16, Q17 or Q18,    -   R⁴ is more preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl or        (C₃-C₆)cycloalkyl,    -   R⁵ is more preferably halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,        (C₁-C₄)haloalkyl-(C₃-C₆)cycloalkyl, cyano-(C₃-C₆)cycloalkyl,        halo-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)alkoxyimino, (C₁-C₄)haloalkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,        (C₁-C₄)haloalkylsulfonyloxy, (C₁-C₄)alkylcarbonyl or        (C₁-C₄)haloalkylcarbonyl,    -   R⁶ is more preferably hydrogen, cyano, halogen, (C₁-C₄)alkyl,        (C₁-C₄)haloalkyl or (C₃-C₆)cycloalkyl,    -   n is more preferably 0, 1 or 2.

Configuration 4

-   -   R¹ is even more preferably methyl, ethyl, n-propyl, isopropyl,        cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl,        fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or        pentafluoroethyl,    -   R² is even more preferably hydrogen, methyl, ethyl, n-propyl,        isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl,        cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl,        fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or        pentafluoroethyl,    -   R³ is even more preferably optionally singly or doubly,        identically or differently substituted cyclopropyl, cyclobutyl,        cyclopentyl or cyclohexyl, where possible substituents in each        case are: methyl, ethyl, n-propyl, i-propyl, cyclopropyl,        difluoromethyl, trifluoromethyl, cyano, fluorine or chlorine,    -   X is even more preferably Q1, Q2, Q3, Q10, Q11, Q13, Q14, Q15 or        Q17,    -   R⁴ is even more preferably methyl, ethyl, n-propyl, isopropyl,        n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl,    -   R⁵ is even more preferably fluorine, chlorine, fluoromethyl,        difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl,        trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,        trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,        trifluoromethylthio, trifluoromethylsulfonyl or        trifluoromethylsulfinyl,    -   R⁶ is even more preferably hydrogen, cyano, methyl,        trifluoromethyl, fluorine or chlorine,    -   n is even more preferably 0, 1 or 2.

Configuration 5-1

-   -   R¹ is particularly ethyl,    -   R² is particularly methyl,    -   R³ is particularly cyclopropyl (unsubstituted),    -   X is particularly Q2,    -   R⁴ is particularly methyl,    -   R⁵ is particularly trifluoromethyl,    -   R⁶ is particularly hydrogen,    -   n is particularly 0 or 2.

Configuration 5-2

-   -   R¹ is particularly ethyl,    -   R² is particularly methyl, ethyl or i-propyl,    -   R³ is particularly cyclopropyl (unsubstituted) or optionally        singly or doubly, identically or differently substituted        cyclohexyl, where possible substituents are: methyl or        trifluoromethyl,    -   X is particularly Q2, Q3, Q13, Q14 or Q15,    -   R⁴ is particularly methyl,    -   R⁵ is particularly trifluoromethyl, trifluoromethoxy,        trifluoromethylthio, trifluoromethylsulfinyl or        trifluoromethylsulfonyl,    -   R⁶ is particularly hydrogen,    -   n is particularly 0 or 2.

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is

and R¹, R², R³ and n have the definitions described in configuration (1)or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is

and R¹, R², R³ and n have the definitions described in configuration (1)or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is

and R¹, R², R³ and n have the definitions described in configuration (1)or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is

and R¹, R², R³ and n have the definitions described in configuration (1)or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is

and R¹, R², R³ and n have the definitions described in configuration (1)or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q2 and R¹, R², R³, R⁴, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q3 and R¹, R², R³, R⁴, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q13 and R¹, R², R³, R⁴, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q14 and R¹, R², R³, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q15 and R¹, R², R³, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q2, Q3, Q13, Q14 or Q15 and R¹, R², R³, R⁴, R⁵,R⁶ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where R³ is cyclopropyl and X, R¹, R², R⁴, R⁵, R⁶ and n havethe definitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where R³ is optionally singly or doubly, identically ordifferently substituted cyclohexyl, where possible substituents are:methyl or trifluoromethyl and X, R¹, R², R⁴, R⁵, R⁶ and n have thedefinitions described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q2, R³ is cyclopropyl, R⁶ is hydrogen and R¹, R²,R⁴, R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q3, R³ is cyclopropyl, R⁶ is hydrogen and R¹, R²,R⁴, R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q3, R³ is optionally singly or doubly,identically or differently substituted cyclohexyl, where possiblesubstituents are: methyl or trifluoromethyl, R⁶ is hydrogen and R¹, R²,R⁴, R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q13, R³ is cyclopropyl, R⁶ is hydrogen and R¹,R², R⁴, R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q14, R³ is cyclopropyl, R⁶ is hydrogen and R¹,R², R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In a preferred embodiment, the invention relates to compounds of theformula (I) where X is Q15, R³ is cyclopropyl, R⁶ is hydrogen and R¹,R², R⁵ and n have the definitions described in configuration (1) orconfiguration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2).

In the definitions listed in general or within areas of preference,unless stated otherwise, halogen is selected from the group of fluorine,chlorine, bromine and iodine, preferably in turn from the group offluorine, chlorine and bromine.

Aryl (including as part of a larger unit, for example arylalkyl), unlessdefined differently elsewhere, is selected from the group of phenyl,naphthyl, anthryl, phenanthrenyl, and is in turn preferably phenyl.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. Among these, preference is given toC₃-C₆-alkynyl radicals and particular preference to C₃-C₄-alkynylradicals. The alkynyl radical may also contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Halogen here is fluorine, chlorine, bromine or iodine,especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

The radical definitions or illustrations given in general terms orlisted within ranges of preference apply correspondingly to end productsand to starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference is given in accordance with the invention to using compoundsof the formula (I) in which there is a combination of the definitionslisted above as being preferred.

Particular preference is given in accordance with the invention to usingcompounds of the formula (I) in which there is a combination of thedefinitions listed above as being more preferred.

Very particular preference is given in accordance with the invention tousing compounds of the formula (I) in which there is a combination ofthe definitions listed above as being even more preferred.

Special preference is given in accordance with the invention to usingcompounds of the formula (I) in which there is a combination of thedefinitions listed as particular definitions.

Depending on the nature of the substituents, the compounds of theformula (I) may take the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassesboth pure stereoisomers and any desired mixtures of these isomers.

The inventive compounds of the formula (I) can be obtained by theprocesses shown in the following schemes:

Process A

The general process for the preparation of compounds of the formula (I)in which R³ is cyclopropyl or cyclobutyl—optionally substituted asdescribed above—and X is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q13 or Q16is described by way of example hereinafter with reference to compoundsof the formula (I) in which X is Q2, Q5 or Q8.

The R¹, R², R⁵ and R⁶ radicals have the definitions described above. Ais —N—R⁴, O or S, where R⁴ has the definition described above. X¹ and X²are halogen. R⁷ is (C₁-C₄)alkyl. R³ is cyclopropyl orcyclobutyl—optionally substituted as described above.

Step a)

Compounds of the formula (III) can be prepared from imidazolederivatives of the formula (II) for example by reaction with ahalogenating reagent, for example N-bromosuccinimide (NBS), in asolvent, for example tetrahydrofuran, or by reaction of compounds of theformula (II) with NBS in combination with azobis(isobutyronitrile)(AIBN) in tetrachloromethane or chloroform, for example analogously tothe processes described in WO2013/149997, WO2014/115077 orWO2011/123609.

Imidazole derivatives of the formula (II) are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in WO2014/191894, US2003/229079 orWO2013/156608.

Step b)

Compounds of the formula (III) in which X¹ is preferably halogen fromthe group of chlorine and bromine can be converted to compounds of theformula (IV), for example by transition metal-mediated cross-couplings[cf. Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695;Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F.Diederich), 2nd ed., Wiley-VCH, Weinheim, 2004] or by nucleophilicaromatic substitution (cf. the processes described in Bioorganic andMedicinal Chemistry Letters 2007, 17, 5825-5830 or U.S. Pat. No.4,125,726).

For example, it is possible to react compounds of the formula (III) inwhich X¹ is preferably chlorine or bromine with suitable boronic acids[R³—B(OH)₂] or boronic esters by known methods (cf. WO2012/143599,US2014/94474, US2014/243316, US2015/284358 or Journal of OrganicChemistry 2004, 69, 8829-8835) in the presence of suitable catalystsfrom the group of the transition metal salts to give compounds of theformula (IV). Preferred examples of coupling catalysts include palladiumcatalysts such as[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II),bis(triphenylphosphine)-palladium(II) dichloride ortetrakis(triphenylphosphine)palladium. Suitable basic reactionauxiliaries for performance of the processes preferably includecarbonates of sodium, potassium or caesium. Some of the boronic acidderivatives [R³—B(OH)₂] or boronic ester derivatives required are knownand/or commercially available, or they can be prepared by commonly knownmethods (cf. Boronic Acids (eds.: D. G. Hall), 2nd ed., Wiley-VCH,Weinheim, 2011). This reaction is preferably effected in a mixture ofwater and an organic solvent selected from customary solvents that areinert under the prevailing reaction conditions. Ethers are frequentlyused, for example tetrahydrofuran, dioxane or 1,2-dimethoxyethane.

Step c)

Imidazole derivatives of the formula (V) in which X² is preferablyhalogen from the group of bromine or iodine can be prepared usingstandard methods from compounds of the formula (IV) by reaction with,for example, bromine or N-bromosuccinimide (NBS), (cf. WO2009/115572 orWO2010/91411) or N-iodosuccinimide (NIS), optionally in the presence ofacetic acid or trifluoroacetic acid (cf. WO2008/63287, WO2007/87548 orWO2009/152025).

Step d)

Compounds of the formula (V) in which X² is preferably halogen from thegroup of bromine or iodine can be converted to compounds of the formula(VI), for example under basic conditions by reaction with mercaptanderivatives (R¹—SH) and copper(I) salts (cf. EP257918 or WO2009/152025)or by nucleophilic aromatic substitution (cf. Australian Journal ofChemistry 1987, 40, 1415-1425).

Alternatively, the reaction of compounds of the formula (V) in which X²is preferably halogen from the group of bromine or iodine with mercaptanderivatives (R¹—SH) can be conducted in the presence of palladiumcatalysts, for example tris(dibenzylideneacetone)dipalladium[Pd₂(dba)₃]. This is frequently accomplished by employing amine bases,for example triethylamine or N,N-diisopropylethylamine (DIPEA), andphosphine ligands, for example Xantphos (cf. WO2013/25958, WO2013/66869,US2009/27039, WO2011/58149, WO2011/143466 or Bioorganic and MedicinalChemistry Letters 2016, 26, 2984-2987). This reaction is preferablyeffected in a solvent selected from customary solvents that are inertunder the prevailing reaction conditions. Preference is given to ethers,for example dioxane or 1,2-dimethoxyethane.

Mercaptan derivatives, for example methyl mercaptan, ethyl mercaptan orisopropyl mercaptan are either commercially available or can be preparedby known methods, for example analogously to the processes described inUS2006/25633, US2006/111591, U.S. Pat. No. 2,820,062, ChemicalCommunications, 13 (2000), 1163-1164 or Journal of the American ChemicalSociety, 44 (1922), 1323-1333.

Step e)

Esters of the formula (VI) can be converted to carboxylic acids of theformula (VII) using standard methods (cf., for example, WO2014/191894,US2006/194779, WO2014/86663 or European Journal of Organic Chemistry2009, 213-222), for example with an alkali metal hydroxide as base, suchas sodium hydroxide or lithium hydroxide, in an alcohol as solvent, forexample methanol or ethanol.

Step f)

Compounds of the formula (I, n=0) can be prepared from compounds of theformulae (VII) with compounds of the formula (VIII) in the presence of acondensing agent.

Compounds of the formula (VIII) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO 2010/125985, WO 2012/074135, WO 2012/086848, WO2013/018928, WO 2015/000715, WO 2015/121136, WO2016/039441,WO2016/059145, WO2016/071214, WO 2016/169882, WO 2016/169886 orWO2016/124557.

The conversion to compounds of the formula (I, n=0) can be effected neator in a solvent, preference being given to conducting the reaction in asolvent selected from the customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol, ethanolor isopropanol; nitriles, for example acetonitrile or propionitrile;aromatic hydrocarbons, for example toluene or xylene; aprotic polarsolvents, for example N,N-dimethylformamide or N-methylpyrrolidone, ornitrogen compounds, for example pyridine.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

The reaction can be conducted in the presence of a suitable catalyst,for example 1-hydroxybenzotriazole.

The reaction can be carried out in the presence of an acid or a base.

Examples of an acid which can be used in the reaction described aresulfonic acids such as methanesulfonic acid or para-toluenesulfonicacid; carboxylic acids such as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

Step g)

The compounds of the formula (I, n=1 or 2) can be prepared by oxidationof compounds of the formula (I, n=0), for example analogously to theprocesses described in WO 2016/169882 or WO 2016/124557. The oxidationis generally conducted in a solvent. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

Process B

The general process for the preparation of compounds of the formula (I)in which X is Q10, Q11 or Q12 is described hereinafter by way of examplewith reference to compounds of the formula (I), in which X is Q11.

The R¹, R², R³, R⁵ and R⁶ radicals have the definitions described above.X³ is halogen.

Step a)

Carboxylic acids of the formula (VII) can be converted to Weinreb amidesof the formula (IX) in the presence of N,O-dimethylhydroxylaminehydrochloride in the presence of a condensing agent in analogy to theprocesses described in U.S. Pat. No. 9,108,905 or Organic Letters 2009,11, 1023-1026.

The conversion to compounds of the formula (IX) is preferably conductedin a solvent selected from customary solvents which are inert under theprevailing reaction conditions. Preference is given to nitriles, forexample acetonitrile or propionitrile, or aprotic polar solvents, forexample N,N-dimethylformamide or N-methylpyrrolidone.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and1,3-dicyclohexylcarbodiimide, anhydrides such as acetic anhydride andtrifluoroacetic anhydride or isobutyl chloroformate.

The reaction can be conducted in the presence of a base, for exampletriethylamine or N-methylmorpholine.

Step b)

Weinreb amides of the formula (IX) can be converted to ketones of theformula (X) in the presence of methyllithium or a methylmagnesiumhalide, for example methylmagnesium bromide, in analogy to the processesdescribed in Journal of Medicinal Chemistry 1995, 38, 4972-4975 orOrganic Letters 2012, 14, 6158-6161.

The conversion to compounds of the formula (X) is conducted in a solventselected from customary solvents which are inert under the prevailingreaction conditions. Preference is given to ethers, for exampletetrahydrofuran or diethyl ether.

Step c)

Ketones of the formula (X) can be converted to an enolate bydeprotonation with lithium diisopropylamide (LDA) in tetrahydrofuran,for example in analogy to the processes described in Chemistry—AEuropean Journal 2011, 17, 4839-4848. The enolate formed can then beconverted, for example with trimethylsilyl chloride (TMSCl) to silylenol ethers, which are subsequently converted to compounds of theformula (XI) by alpha-halogenation, for example with N-bromosuccinimide(NBS).

Alternatively, proceeding from ketones of the formula (X), it is alsopossible to use other methods known from the literature foralpha-halogenation, for example analogously to the processes describedin US2006/52378, WO2005/7631, US2012/214791 or U.S. Pat. No. 4,544,664.

Step d)

Compounds of the formula (I, n=0) can be prepared by cyclizing thecompounds of the formula (XI) with amines of the formula (XII). Thecyclization is effected, for example, in ethanol, acetonitrile orN,N-dimethylformamide by known methods in analogy to the processesdescribed, for example, in WO2005/66177, WO2012/88411, WO2013/3298,US2009/203705, US2012/258951, WO2012/168733, WO2014/187762 or J. Med.Chem. 1988, 31, 1590-1595.

The compounds of the formula (XII) are commercially available or can beprepared by known methods, for example analogously to the processesdescribed in US2009/170849, WO2016/51193, WO2016/107742 or WO2016/71214.

Step e)

The conversion of compounds of the formula (I, n=0) to compounds of theformula (I, n=1 or 2) is effected analogously to process A, step g).

Process C

The general process for the preparation of compounds of the formula (I)in which X is Q14, Q15, Q17 or Q18 is described by way of examplehereinafter with reference to compounds of the formula (I) in which X isQ14.

The R¹, R², R³, R⁵ and R⁶ radicals have the definitions described above.X⁴ and X⁵ are halogen.

The sequence of steps b) to e) can be varied.

Step a)

Imidazole derivatives of the formula (XIII) can be converted analogouslyto process A, step a) and step c), with a halogenating reagent, forexample NBS, bromine or iodine, to compounds of the formula (XIV)—inwhich X⁴ and X⁵ are preferably halogen from the group of bromine andiodine (cf. WO2011/85269, WO2004/80998 or WO2016/87487).

Compounds of the formula (XIII) are commercially available or can beprepared by known methods, for example analogously to the processesdescribed in Advanced Synthesis and Catalysis 2009, 351, 2912-2920;Synthetic Communications 1989, 19, 2551-2566 or WO2009/27746.

Step b)

Compounds of the formula (XVI) can be synthesized from compounds of theformula (XIV) by reaction with compounds of the formula (XV), forexample by reaction under basic conditions—for example by use ofcarbonate bases such as sodium carbonate or lithium carbonate—in anaprotic polar solvent, for example N,N-dimethylformamide, analogously tothe processes described in Bioorganic and Medicinal Chemistry 2008, 16,9524-9535; Bioorganic and Medicinal Chemistry Letters 1997, 7, 2723-2728or WO2016/20286.

Alternatively, the reaction can be effected in the presence of copper orcopper(I) iodide and basic reaction auxiliaries, for exampletrans-N,N′-dimethylcyclohexane-1,2-diamine, potassium carbonate orpotassium phosphate, in a suitable solvent or diluent, for exampleanalogously to the processes described in WO2016/20286 or KR2015/66012.Useful solvents or diluents include all inert organic solvents, forexample aliphatic or aromatic hydrocarbons. Preference is given here tousing toluene.

Compounds of the formula (XV) are commercially available or can beprepared by known methods, for example analogously to the processdescribed in Organic Letters 2011, 13, 3542-3545.

Step c)

Imidazole derivatives of the formula (XVI) can be converted usingstandard methods (cf., for example, Heterocycles 1999, 50, 1081-1090;WO2009/70045 or Bioorganic and Medicinal Chemistry Letters 2007, 17,1369-1375) by reaction with electrophilic compounds containing a leavinggroup (R²-LG; LG=chlorine, bromine, iodine, O-triflate, O-mesyl) inN-substituted imidazole derivatives of the formula (XVII), for examplewith an alkali metal hydroxide as base, such as sodium hydroxide orpotassium hydroxide, in an alcohol as solvent, for example ethanol.

Step d)

The conversion of compounds of the formula (XVII) to compounds of theformula (I, n=0) is effected analogously to process A, step d).

Step e)

The conversion of compounds of the formula (I, n=0) to compounds of theformula (I, n=1 or 2) is effected analogously to process A, step g).

Process D

The general process for the preparation of compounds of the formula (I)in which X is Q14, Q15, Q17 or Q18 is described by way of examplehereinafter with reference to compounds of the formula (I) in which X isQ14.

The R¹, R², R³, R⁵ and R⁶ radicals have the definitions described above.Boc=tert-butyloxycarbonyl.

Step a)

Imidazole derivatives of the formula (XVIII) can be prepared by knownmethods from compounds of the formula (VII) by reaction with diphenylazidophosphate (DPPA) in tert-butanol in the presence of an amine base,for example triethylamine, for example analogously to the processesdescribed in US2012/149699, WO2011/112766 or WO2009/23179.

Step b)

N-Boc-protected imidazole derivatives of the formula (XVIII) can beconverted to imidazole derivatives of the formula (XIX) using standardmethods (cf., for example, WO2015/166289, US2008/9497 or WO2006/77424)by using an acid, for example hydrochloric acid or trifluoroacetic acid,in a solvent, for example 1,4-dioxane or methanol.

Step c)

Imidazole derivatives of the formula (XIX) can be converted to compoundsof the formula (I, n=0) by reaction with compounds of the formula (XX)by imine formation (for example in toluene or dichloromethane), followedby cyclization with optional use of an acid, for example titaniumtetrachloride or titanium isopropoxide, for example analogously to theprocesses described in WO2012/66061 or Bioorganic and MedicinalChemistry Letters 2017, 27, 1593-1597.

Compounds of the formula (XX) can be prepared in analogy to processesknown from the literature (see, for example, WO2015/116882,WO2017/75694, Angewandte Chemie International Edition 2011, 50,1702-1706 or Organic Letters 2010, 12, 2884-2887).

Step d)

The conversion of compounds of the formula (I, n=0) to compounds of theformula (I, n=1 or 2) is effected analogously to process A, step g).

Process E

The general process for the preparation of compounds of the formula (I)in which R³ is cyclopropyl or cyclobutyl—optionally substituted asdescribed above—and X is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q13 or Q16is described by way of example hereinafter with reference to compoundsof the formula (I) in which X is Q2, Q5 or Q8.

The R¹, R², R⁵ and R⁶ radicals have the definitions described above. Ais —N—R⁴, O or S, where R⁴ has the definition described above. X¹ ishalogen. R⁷ is (C₁-C₄)alkyl. R³ is cyclopropyl or cyclobutyl—optionallysubstituted as described above.

Step a)

Compounds of the formula (III) can be prepared from imidazolederivatives of the formula (II), for example by reaction with ahalogenating reagent, for example N-bromosuccinimide (NBS), in asolvent, for example tetrahydrofuran, or by reaction of compounds of theformula (II) with NBS in combination with azobis(isobutyronitrile)(AIBN) in tetrachloromethane or chloroform, for example analogously tothe processes described in WO2013/149997, WO2014/115077 orWO2011/123609.

Imidazole derivatives of the formula (II) are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in WO2014/191894, US2003/229079 orWO2013/156608.

Step b)

Imidazole derivatives of the formula (XXI) can be prepared usingstandard methods from compounds of the formula (III) by reaction with adisulfide (R¹—S—S—R¹) and, for example, a strong base, preferablylithium diisopropylamide (LDA), in tetrahydrofuran (cf. Bioorganic andMedicinal Chemistry Letters 2010, 20, 1084-108) or, for example,hydrogen peroxide and iodine in ethanol (cf. Synthesis 2015, 47,659-671).

Step c)

The conversion of compounds of the formula (XXI) to compounds of theformula (XXII) is effected analogously to process A, step e).

Step d)

The reaction of compounds of the formula (XXII) with compounds of theformula (VIII) to give compounds of the formula (XXIII) is effectedanalogously to process A, step f).

Step e,h)

The conversion of compounds of the formula (XXIII) to compounds of theformula (XXIV) and the conversion of compounds of the formula (I, n=0)to compounds of the formula (I, n=1 or 2) is effected analogously toprocess A, step g).

Step f,g)

The conversion of compounds of the formula (XXIII) to compounds of theformula (I, n=0) and the conversion of compounds of the formula (XXIV)to compounds of the formula (I, n=1 or 2) is effected analogously toprocess A, step b).

Proceeding from compounds of the formula (XXII), it is possible inanalogy to process B with subsequent conduction of steps e)→f) or g)→h)from process E also to prepare compounds of the formula (I) in which Xis Q10, Q11 or Q12.

Process F

The general process for the preparation of compounds of the formula (I)in which R³ is cyclopentyl or cyclohexyl—optionally substituted asdescribed above—and X is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q13 or Q16is described by way of example hereinafter with reference to compoundsof the formula (I) in which R³ is cyclohexyl and X is Q2, Q5 or Q8.

The R¹, R², R⁵ and R⁶ radicals have the definitions described above. Ais —N—R⁴, O or S, where R⁴ has the definition described above. X¹ ishalogen.

Step a)

Compounds of the formula (XXV) can be prepared from compounds of theformula (XXIII) and compounds of the formula (XXVI) can be prepared fromcompounds of the formula (XXIV), for example analogously to process A,step b), by using appropriate cyclohexenyl- and cyclopentenylboronicacids or cyclohexenyl- and cyclopentenylboronic esters.

Cyclohexenyl- and cyclopentenylboronic acids or cyclohexenyl- andcyclopentenylboronic esters are either commercially available or can beprepared by known methods, for example analogously to the processesdescribed in WO2009/111056, WO2016/128529 or US2011/166163.

Step b)

Compounds of the formula (I) can be prepared using standard methods fromcompounds of the formulae (XXV or XXVI) in a solvent (e.g. ethyl acetateor methanol) by using a hydrogenation catalyst (for example palladium oncharcoal or platinum dioxide) and reaction with hydrogen (cf.US2008/318935, US2011/275801 or WO2015/91584).

Process G

The general process for the preparation of compounds of the formula (I)in which R³ is cyclopentyl or cyclohexyl—optionally substituted asdescribed above—and X is Q10, Q11, Q12, Q14, Q15, Q17 or Q18 isdescribed by way of example hereinafter with reference to compounds ofthe formula (I) in which R³ is cyclohexyl.

The R² radical has the definitions described above. X¹ is halogen. R⁷ is(C₁-C₄)alkyl.

Step a)

The conversion of compounds of the formula (III) to compounds of theformula (XXVII) is effected analogously to process F, step a).

Step b)

The conversion of compounds of the formula (XXVII) to compounds of theformula (IV) is effected analogously to process F, step b).

The further conversion of compounds of the formula (IV) to compounds ofthe formula (I) is effected analogously to processes A, B and D.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablycarried out in agriculture and forestry, and in material protection.This preferably excludes methods for surgical or therapeutic treatmentof the human or animal body and diagnostic methods carried out on thehuman or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection compositions.

In the context of the present application, the term “pesticide” in eachcase also always encompasses the term “crop protection composition”.

The compounds of the formula (I), given good plant tolerance, favourableendotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, especially nematodes and molluscs, which areencountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are carried outon the human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stables, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of the formula (I) can preferably be used as pesticides.They are active against normally sensitive and resistant species andalso against all or specific stages of development. The abovementionedpests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., e.g. Acarus siro, Aceria kuko,Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculusschlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp.,Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobiagraminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoidesfarinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychushicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychusbanksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus,Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum,Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus,Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi,Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychuscitri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, e.g. Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g.Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agrilus spp., for example Agrilus planipennis, Agrilus coxalis,Agrilus bilineatus, Agrilus anxius, Agriotes spp., for example Agrioteslinneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallonsolstitialis, Anobium punctatum, Anoplophora spp., for exampleAnoplophora glabripennis, Anthonomus spp., for example Anthonomusgrundis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., forexample Atomaria linearis, Attagenus spp., Baris caerulescens,Bruchidius obtectus, Bruchus spp., for example Bruchus pisorum, Bruchusrufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., forexample Ceutorrhynchus assimilis, Ceutorrhynchus quadridens,Ceutorrhynchus rapae, Chaetocnema spp., for example Chaetocnemaconfinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus,Conoderus spp., Cosmopolites spp., for example Cosmopolites sordidus,Costelytra zealundica, Ctenicera spp., Curculio spp., for exampleCurculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dendroctonus spp., for exampleDendroctonus ponderosae, Dermestes spp., Diabrotica spp., for exampleDiabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctatahowardi, Diabrotica undecimpunctata undecimpunctata, Diabroticavirgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp.,Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.,for example Epilachna borealis, Epilachna varivestis, Epitrix spp., forexample Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., for example Hypothenemus hampei,Hypothenemus obscurus, Hypothenemus pubescens, Lachnosternaconsanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp.,Lema spp., Leptinotarsa decemlineata, Leucoptera spp., for exampleLeucoptera coffeella, Limonius ectypus, Lissorhoptrus oryzophilus,Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorphaxanthodera, Lyctus spp., Megacyllene spp., for example Megacyllenerobiniae, Megascelis spp., Melanotus spp., for example Melanotuslongulus oregonensis, Meligethes aeneus, Melolontha spp., for exampleMelolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., for example Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., for example Phyllotretaarmoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotretastriolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus,Psylliodes spp., for example Psylliodes affinis, Psylliodeschrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis,Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus,Rhynchophorus palmarum, Scolytus spp., for example Scolytusmultistriatus, Sinoxylon perforans, Sitophilus spp., for exampleSitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophiluszeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., forexample Sternechus paludatus, Symphyletes spp., Tanymecus spp., forexample Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus,Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;

from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., for example Liriomyza brassicae,Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for exampleLucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for exampleMusca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyiaspp., for example Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., forexample Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta,Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex, Toxotrypana curvicauda;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., e.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., e.g. Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma pini, Aphis spp., e.g. Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani,Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae,Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae,Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata,Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera,Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspistegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila,Coccomytilus halli, Coccus spp., e.g. Coccus hesperidum, Coccuslongulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis,Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodeschittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp.,Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g.Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccusspp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g.Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g.Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., e.g. Lecanium corni (=Parthenolecaniumcorni), Lepidosaphes spp., e.g. Lepidosaphes ulmi, Lipaphis erysimi,Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g.Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi,Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxyachinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g.Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigusbursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp.,Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psyllaspp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta,Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus,Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespulaspp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g.Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema(Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp.,Paravespula spp., Plagiolepis spp., Sirex spp., e.g. Sirex noctilio,Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp.,Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., e.g.Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g.Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedialeucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabamaspp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp.,Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp.,Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chiloplejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp.,Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana,Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp.,Diatraea saccharalis, Dioryctria spp., e.g. Dioryctria zimmermani,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia spp., e.g. Ephestia elutella, Ephestia kuehniella,Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviellamusculana, Etiella spp., Eudocima spp., Eulia spp., Eupoeciliaambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp.,e.g. Grapholita molesta, Grapholita prunivora, Hedylepta spp.,Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpa zea, Heliothisspp., e.g. Heliothis virescens Hofmannophila pseudospretella, Homoeosomaspp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata,Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis,Leucoptera spp., e.g. Leucoptera coffeella, Lithocolletis spp., e.g.Lithocolletis blancardella, Lithophane antennata, Lobesia spp., e.g.Lobesia botrana, Loxagrotis albicosta, Lymantria spp., e.g. Lymantriadispar, Lyonetia spp., e.g. Lyonetia clerkella, Malacosoma neustria,Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp.,Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphulaspp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthagaspp., Ostrinia spp., e.g. Ostrinia nubilalis, Panolis flammea, Parnaraspp., Pectinophora spp., e.g. Pectinophora gossypiella, Perileucopteraspp., Phthorimaea spp., e.g. Phthorimaea operculella, Phyllocnistiscitrella, Phyllonorycter spp., e.g. Phyllonorycter blancardella,Phyllonorycter crataegella, Pieris spp., e.g. Pieris rapae, Platynotastultana, Plodia interpunctella, Plusia spp., Plutella xylostella(=Plutella maculipennis), Podesia spp., e.g. Podesia syringae, Praysspp., Prodenia spp., Protoparce spp., Pseudaletia spp., e.g. Pseudaletiaunipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu,Schoenobius spp., e.g. Schoenobius bipunctifer, Scirpophaga spp., e.g.Scirpophaga innotata, Scotia segetum, Sesamia spp., e.g. Sesamiainferens, Sparganothis spp., Spodoptera spp., e.g. Spodoptera eradiana,Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedonspp., Tecia solanivora, Thaumetopoea spp., Thermesia gemmatalis, Tineacloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp.,Trichophaga tapetzella, Trichoplusia spp., for example Trichoplusia ni,Tryporyza incertulas, Tuta absoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria,Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca,Frankliniella occidentalis, Frankliniella schultzei, Frankliniellatritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothripsspp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., e.g. Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., e.g.Scutigerella immaculata;

pests from the phylum of the Mollusca, for example from the class of theBivalvia, e.g. Dreissena spp.;

and also from the class of the Gastropoda, for example Anion spp., e.g.Anion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g.Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomaceaspp., Succinea spp.;

plant pests from the phylum of the Nematoda, i.e. plant-parasiticnematodes, in particular Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., for example Longidorus africanus,Meloidogyne spp., for example Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., for example Paratrichodorus minor, Paratylenchusspp., Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

The compounds of the formula (I) can, as the case may be, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active ingredients.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I).Optionally, the use forms comprise further pesticides and/or adjuvantswhich improve action, such as penetrants, e.g. vegetable oils, forexample rapeseed oil, sunflower oil, mineral oils, for example paraffinoils, alkyl esters of vegetable fatty acids, for example rapeseed oilmethyl ester or soya oil methyl ester, or alkanol alkoxylates and/orspreaders, for example alkylsiloxanes and/or salts, for example organicor inorganic ammonium or phosphonium salts, for example ammonium sulfateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulfosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further active agrochemical ingredients.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for example by mixingthe compounds of the formula (I) with auxiliaries, for exampleextenders, solvents and/or solid carriers and/or other auxiliaries, forexample surfactants. The formulations are produced either in suitablefacilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed-dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulfones andsulfoxides (such as dimethyl sulfoxide).

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Useful liquid solvents areessentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, for example chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, for example cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, for examplemethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones, for example acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents, for exampledimethyl sulfoxide, and water.

In principle, it is possible to use all suitable carriers. Suitablecarriers include more particularly the following: e.g. ammonium saltsand natural, finely ground rocks, such as kaolins, aluminas, talc,chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, andsynthetic, finely ground rocks, such as highly disperse silica,aluminium oxide and natural or synthetic silicates, resins, waxes and/orsolid fertilizers. It is likewise possible to use mixtures of suchcarriers. Useful carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic flours, andalso granules of organic material such as sawdust, paper, coconutshells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonicacid, polycondensates of ethylene oxide with fatty alcohols or withfatty acids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulfosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulfates, sulfonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulfonates,alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite wasteliquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and if the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulfosuccinate, or increaseviscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of active agrochemicalingredients into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and hence toincrease the mobility of the active ingredients in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulfate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active ingredient combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessibility of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active ingredients or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties, for example growth, yieldand quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active ingredients specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators, for example pyrethroids, e.g.acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrinor DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, forexample neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, forexample spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, forexample avermectins/milbemycins, e.g. abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone mimetics, for example juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multisite) inhibitors, for example alkylhalides, e.g. methyl bromide and other alkyl halides; or chloropicrin orsulfuryl fluoride or borax or tartar emetic or methyl isocyanategenerator, e.g. diazomet and metam.

(9) Chordotonal organ modulators, e.g. pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect midgut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andB.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A,mCry3A, Cry3Ab, Cry3Bb, Cry34 Ab1/35Ab1; or

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors,for example diafenthiuron or organotin compounds, e.g. azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors (especially in the case of Diptera), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, for example amitraz.

(20) Mitochondrial complex III electron transport inhibitors, forexample hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarbor metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, for examplephosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide, or cyanides, calcium cyanide, potassium cyanide andsodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for examplebeta-keto nitrile derivatives, e.g. cyenopyrafen and cyflumetofen andcarboxanilides, for example pyflubumide.

(28) Ryanodine receptor modulators, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active ingredients, for example afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus finnus (I-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg. No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamideand(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazole-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) andN-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxamide(known from CN 103265527 A) (CAS 1452877-50-7).

Fungicides

The active ingredients specified herein by their common name are knownand described, for example, in “Pesticide Manual” (16th Ed. British CropProtection Council) or on the internet (for example:http://www.alanwood.net/pesticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components mentioned in classes (1) to (15), as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062)5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.081) mefentrifluconazole, (1.082) ipfentrifluconazole.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain in complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.029) methyl{5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds having capacity for multisite activity, for example (5.001)Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram, (5.023)6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulphonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.062)5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM 1-1562 or Bacillus finnus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (accessionnumber CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) is effected directly or by allowing thecompounds to act on the surroundings, the habitat or the storage spacethereof by the customary treatment methods, for example by dipping,spraying, evaporating, fogging, scattering, painting on, injecting, and,in the case of propagation material, especially in the case of seeds,also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better capability for storage and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants to animal and microbial pests, such as insects, arachnids,nematodes, mites, slugs and snails, owing, for example, to toxins formedin the plants, in particular those formed in the plants by the geneticmaterial from Bacillus thuringiensis (for example by the genes CryIA(a),CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb andCryIF and also combinations thereof), and also increased resistance ofthe plants to phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certain activeherbicidal compounds, for example imidazolinones, sulfonylureas,glyphosate or phosphinothricin (for example the “PAT” gene). The geneswhich impart the desired properties (“traits”) in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants mentioned include the important cropplants, such as cereals (wheat, rice, triticale, barley, rye, oats),maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas andother types of vegetable, cotton, tobacco, oilseed rape and also fruitplants (the fruits being apples, pears, citrus fruits and grapevines),particular emphasis being given to maize, soya beans, wheat, rice,potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application,meaning that the compounds of the formula (I) are applied to thefoliage, in which case the treatment frequency and the application rateshould be adjusted according to the level of infestation with the pestin question.

In the case of systemically active ingredients, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I)according to the invention are introduced in solid form (e.g. in theform of granules) into the locus of the plants. In the case of paddyrice crops, this can also be accomplished by metering the compound ofthe formula (I) in a solid application form (for example as granules)into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active ingredient used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active ingredient used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and also the germinating plant with aminimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) according to the invention for protectionfrom animal pests. The invention also relates to seed which has beentreated simultaneously with a compound of the formula (I) and a mixingcomponent. The invention further relates to seed which has been treatedat different times with a compound of the formula (I) and a mixingcomponent. In the case of seed which has been treated at different timeswith a compound of the formula (I) and a mixing component, theindividual substances may be present on the seed in different layers. Inthis case, the layers comprising a compound of the formula (I) andmixing components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of the formula(I) and a mixing component have been applied as part of a coating or asa further layer or further layers in addition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occur when a compound of the formula (I) actssystemically is that the treatment of the seed protects not only theseed itself but also the plants resulting therefrom, after emergence,from animal pests. In this way, the immediate treatment of the crop atthe time of sowing or shortly thereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for the protection of seedof any plant variety which is used in agriculture, in greenhouses, inforests or in horticulture. More particularly, this is the seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugar beets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for treatment of transgenic seed which comprisesat least one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been soaked, for example in water, untilit reaches a certain stage of the rice embryo (“pigeon breast stage”)which results in stimulation of germination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activeingredients which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives, for examplecustomary extenders and solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefromthrough the addition of water, all mixing units usable customarily forthe seed dressing are useful. Specifically, the procedure in seeddressing is to place the seed into a mixer in batchwise or continuousoperation, to add the particular desired amount of seed-dressingformulations, either as such or after prior dilution with water, and tomix until the formulation is distributed homogeneously on the seed. Ifappropriate, this is followed by a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasite”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects or acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable endotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds; reptiles, amphibians or aquarium fish.

In a specific embodiment, the compounds of the formula (I) areadministered to mammals.

In another specific embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds or particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of theformula (I) are effective in reducing the incidence of the particularparasite in an animal infected with such parasites to an innocuousdegree. More specifically, “controlling” in the present context meansthat the compounds of the formula (I) kill the respective parasite,inhibit its growth, or inhibit its proliferation.

The arthropods include, for example, but are not limited to,

from the order of Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order Mallophagida and the suborders Amblycerina andIschnocerina, for example Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

from the order of Siphonapterida, for example, Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

from the order of heteropterida, for example, Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

In addition, in the case of the arthropods, mention should be made byway of example, without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae such as Argas spp., Ornithodorusspp., Otobius spp., from the family of Ixodidae such as Amblyomma spp.,Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp.,Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genusof multi-host ticks); from the order of Mesostigmata such as Dermanyssusspp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp.,Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the order of theActinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp.,Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example, Acarus spp.,Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp.,Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp.,Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (Flagellata), such as:

Metamonada: from the order of Diplomonadida, for example, Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example, Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example, Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for exampleEntamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order of Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida, forexample, Hepatozoon spp., Klossiella spp.; from the order ofHaemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from theorder of Piroplasmida, for example, Babesia spp., Ciliophora spp.,Echinozoon spp., Theileria spp.; from the order of Vesibuliferida, forexample, Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and also, for example, Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, nematodes, Pentastoma and Platyhelminthes (e.g.Monogenea, cestodes and trematodes).

Exemplary helminths include, but are not limited to:

Monogenea: e.g. Dactylogyrus spp., Gyrodactylus spp., Microbothriumspp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic, metaphylacticor therapeutic.

Thus, one embodiment of the present invention relates to the compoundsof the formula (I) for use as a medicament.

A further aspect relates to the compounds of the formula (I) for use asan antiendoparasitic agent.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antithelminthic agent, especially for useas a nematicide, platyhelminthicide, acanthocephalicide orpentastomicide.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antiprotozoic agent.

A further aspect relates to the compounds of the formula (I) for use asan antiectoparasitic agent, especially an arthropodicide, veryparticularly an insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of the formula(I) and at least one of the following: a pharmaceutically acceptableexcipient (e.g. solid or liquid diluents), a pharmaceutically acceptableauxiliary (e.g. surfactants), especially a pharmaceutically acceptableexcipient used conventionally in veterinary medicine formulations and/ora pharmaceutically acceptable auxiliary conventionally used inveterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of the formula (I) withpharmaceutically acceptable excipients and/or auxiliaries, especiallywith pharmaceutically acceptable excipients used conventionally inveterinary medicine formulations and/or auxiliaries used conventionallyin veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidaland acaricidal formulations, according to the aspects mentioned, andmethods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of the formula (I) in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of the formula (I) inthe treatment of a parasite infection, especially an infection caused bya parasite selected from the group of the ectoparasites andendoparasites mentioned here, in an animal, especially a nonhumananimal.

In the present context of animal health or veterinary medicine, the term“treatment” includes prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of the formula (I) with other active ingredients, especiallywith endo- and ectoparasiticides, are provided for the field ofveterinary medicine.

In the field of animal health, “mixture” means not just that two (ormore) different active ingredients are formulated in a commonformulation and are correspondingly employed together, but also relatesto products comprising formulations separated for each activeingredient. Accordingly, when more than two active ingredients are to beemployed, all active ingredients can be formulated in a commonformulation or all active ingredients can be formulated in separateformulations; likewise conceivable are mixed forms in which some of theactive ingredients are formulated together and some of the activeingredients are formulated separately. Separate formulations allow theseparate or successive application of the active ingredients inquestion.

The active ingredients specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.:http://www.alanwood.net/pesticides).

Illustrative active ingredients from the group of the ectoparasiticidesas mixing components include, without any intention that this shouldconstitute a restriction, the insecticides and acaricides listed indetail above. Further usable active ingredients are listed below inaccordance with the abovementioned classification based on the currentIRAC Mode of Action Classification Scheme: (1) acetylcholinesterase(AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodiumchannel modulators; (4) nicotinic acetylcholine receptor (nAChR)competitive modulators; (5) nicotinic acetylcholine receptor (nAChR)allosteric modulators; (6) glutamate-gated chloride channel (GluCl)allosteric modulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators;

active ingredients having unknown or non-specific mechanisms of action,e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulfone, isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos,aromfenvinfos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl),fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos,flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor;or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner;

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs),

neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active ingredients from the group of the endoparasiticides,as mixing components, include, but are not limited to, activeanthelmintic ingredients and active antiprotozoic ingredients.

The anthelmintically active ingredients include but are not limited tothe following nematicidally, trematicidally and/or cestocidally activeingredients:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulfoxide, albendazole,flubendazole;

from the class of the depsipeptides, preferably cyclic depsipeptides,especially 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel;

from the class of the piperazines, for example: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic ingredients include, but are not limited to, thefollowing active ingredients:

from the class of the triazines, for example: diclazuril, ponazuril,letrazuril, toltrazuril;

from the class of polyether ionophores, for example: monensin,salinomycin, maduramicin, narasin;

from the class of the macrocyclic lactones, for example: milbemycin,erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquine;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulfonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquin, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) onto a host or after injection into a host (for example malariaparasites by mosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia bungdorferi sensu lato., Borreliaduttoni, tick-borne encephalitis, Q fever (Coxiella burnetii),babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders of Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) take the formof a ready-to-use pesticide, meaning that they can be applied to thematerial in question without further modifications. Useful furtherinsecticides or fungicides especially include those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active ingredients, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids, ticks and mites encountered in enclosed spaces, forexample dwellings, factory halls, offices, vehicle cabins, animalbreeding facilities. For controlling animal pests, the compounds of theformula (I) are used alone or in combination with other activeingredients and/or auxiliaries. They are preferably used in domesticinsecticide products. The compounds of the formula (I) are effectiveagainst sensitive and resistant species, and against all developmentalstages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES Ethyl 2-bromo-1-methyl-1H-imidazol-4-carboxylate

30 g (193.5 mmol) of ethyl 1-methyl-1H-imidazole-4-carboxylate weredissolved in 500 ml of tetrahydrofuran and cooled to 0° C. To thissolution were added 34.5 g (193.5 mmol) of NBS in portions, and thereaction mixture was stirred at room temperature overnight. The reactionwas ended by the addition of saturated sodium thiosulfate solution(Na₂S₂O₃), and 800 ml of ethyl acetate were added. The phases wereseparated and extraction was effected three times with 800 ml each timeof ethyl acetate. The organic phases were combined, dried over sodiumsulfate and filtered. The solvent was distilled off under reducedpressure and the residue was purified by column chromatographypurification with a petroleum ether/ethyl acetate gradient (3:1) aseluent.

¹H NMR (300 MHz, D₆-DMSO) δ ppm: 1.26 (t, 3H), 3.64 (s, 3H), 4.22 (q,2H), 8.07 (s, 1H).

Ethyl 2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate

To a solution of 4 g (17.17 mmol) of ethyl2-bromo-1-methyl-1H-imidazole-4-carboxylate in tetrahydrofuran (40 ml)and water (15 ml) were added, and a nitrogen atmosphere, 602 mg (0.85mmol) of bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh₃)₂Cl₂),11.2 g (34.3 mmol) of caesium carbonate and 4.43 g (51.51 mmol) ofcyclopropylboronic acid. The mixture was heated to 80° C., and a further4.43 g (51.51 mmol) of cyclopropylboronic acid (dissolved in 20 ml oftetrahydrofuran) were added. The reaction mixture was stirred at 80° C.overnight. Subsequently, it was cooled to room temperature and extractedtwice with 200 ml each time of ethyl acetate. The organic phases werecombined, dried over sodium sulfate and filtered. The solvent wasdistilled off under reduced pressure and the residue was purified bycolumn chromatography purification with a petroleum ether/ethyl acetategradient (1:1) as eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 0.80-0.85 (m, 2H), 0.86-0.93 (m, 2H),1.23 (t, 3H), 1.93-2.00 (m, 1H), 3.69 (s, 3H), 4.16 (q, 2H), 7.75 (s,1H).

Ethyl 2-cyclopropyl-5-iodo-1-methyl-1H-imidazole-4-carboxylate

To a solution of 350 mg (1.80 mmol) of ethyl2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate in acetic acid (15 ml)were added 620 mg (3.50 mmol) of N-iodosuccinimide (NIS). The mixturewas stirred at room temperature overnight. Subsequently, the reactionmixture was concentrated under reduced pressure and saturated sodiumthiosulfate solution was added. The solution was adjusted to pH=7-8 byaddition of saturated sodium hydrogencarbonate solution. Then extractionwas effected twice with 50 ml each time of ethyl acetate. The organicphases were combined, dried over sodium sulfate and filtered. Thesolvent was distilled off under reduced pressure and the residue waspurified by preparative thin-layer chromatography with a petroleumether/ethyl acetate gradient (2:1) as eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 0.81-0.84 (m, 2H), 0.91-0.95 (m, 2H),1.26 (t, 3H), 2.09 (m, 1H), 3.67 (s, 3H), 4.19 (q, 2H).

Ethyl2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylate

To a solution of 300 mg (0.94 mmol) of ethyl2-cyclopropyl-5-iod-1-methyl-1H-imidazole-4-carboxylate in 1,4-dioxane(15 ml) were added 116 mg (1.88 mmol) of ethanethiol, 364 mg (2.82 mmol)of N,N-diisopropylethylamine (DIPEA), 55 mg (0.05 mmol) oftris(dibenzylideneacetone)-dipalladium(0)-chloroform adduct[Pd₂(dba)₃.CHCl₃] and 55 mg (0.1 mmol) of Xantphos. The mixture wasstirred at 100° C. overnight. Subsequently, the reaction mixture wascooled down to room temperature and water was added to the mixture. Thenextraction was effected twice with ethyl acetate. The organic phaseswere combined, dried over sodium sulfate and filtered. The solvent wasdistilled off under reduced pressure and the residue was purified bypreparative thin-layer chromatography with a petroleum ether/ethylacetate gradient (1:1) as eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 0.82-0.98 (m, 4H), 1.08 (t, 3H), 1.26(t, 3H), 2.00-2.10 (m, 1H), 2.80 (q, 2H), 3.70 (s, 3H), 4.21 (q, 2H).

2-Cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylic acid

To a solution of 240 mg (0.94 mmol) of ethyl2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylate inmethanol (6 ml) and water (6 ml) were added 189 mg (4.70 mmol) of sodiumhydroxide. The mixture was stirred at room temperature overnight. Thesolution was adjusted to pH=3-4 by adding concentrated aqueoushydrochloric acid. Subsequently, the reaction mixture was extracted withchloroform. The organic phases were combined, dried over sodium sulfateand filtered. The solvent was distilled off under reduced pressure andthe residue was used in the next synthesis stage without furtherpurification.

2-[2-Cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine(I-1)

To a solution of 200 mg (0.76 mmol) of2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylic acidin pyridine (10 ml) were added 168 mg (0.88 mmol) ofN²-methyl-5-(trifluoromethyl)pyridine-2,3-diamine and 168 mg (0.88 mmol)of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI).The mixture was stirred at 80° C. overnight. Subsequently, the reactionmixture was cooled down to room temperature, water was added andextraction was effected with ethyl acetate. The organic phases werecombined, dried over sodium sulfate and filtered. The solvent wasdistilled off under reduced pressure and the residue was dissolved inacetic acid (15 ml). The mixture was stirred at 100° C. overnight andcooled down to room temperature, water (20 ml) was added and the mixturewas adjusted to pH=7-8 by adding saturated sodium hydrogencarbonatesolution. Then the mixture was extracted twice with ethyl acetate. Theorganic phases were combined and the solvent was distilled off underreduced pressure. The residue was purified by preparative thin-layerchromatography with a petroleum ether/ethyl acetate gradient (3:1) aseluent.

¹H NMR (300 MHz, CDCl₃) δ ppm: 1.00-1.13 (m, 7H), 1.80-1.89 (m, 1H),2.88 (q, 2H), 3.75 (s, 3H), 4.07 (s, 3H), 8.21 (d, 1H), 8.55 (d, 1H).

2-[2-Cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine(I-2)

To a solution of 90 mg (0.23 mmol) of2-[2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridinein dichloromethane (20 ml) were added, at 0° C., 163 mg (0.95 mmol) ofmeta-chloroperbenzoic acid (mCPBA). The mixture was stirred at roomtemperature overnight. Subsequently, the solution was diluted by addingdichloromethane (50 ml) and washed with saturated sodium thiosulfatesolution. The organic phase was removed, dried over sodium sulfate andfiltered. The solvent was distilled off under reduced pressure and theresidue was purified by preparative thin-layer chromatography with apetroleum ether/ethyl acetate gradient (1:1) as eluent.

¹H NMR (300 MHz, CDCl₃) δ ppm: 1.06-1.14 (m, 4H), 1.35 (t, 3H),1.82-1.91 (m, 1H), 3.71 (q, 2H), 3.89 (s, 3H), 3.98 (s, 3H), 8.19 (d,1H), 8.61 (d, 1H).

2-Bromo-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylic acid

31 g (134 mmol) of ethyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate and24.4 g (200 mmol) of diethyl disulfide were dissolved in 620 ml oftetrahydrofuran and cooled to −78° C. To this solution were addeddropwise 100 ml (2M in THF, 200 mmol) of lithium diisopropylamide (LDA),and the reaction mixture was stirred at −78° C. for 30 min. The reactionwas ended by the addition of saturated ammonium chloride solution. Thephases were separated and the aqueous phase was extracted three timeswith 300 ml each time of ethyl acetate. The organic phases werecombined, dried over magnesium sulfate and filtered. The solvent wasdistilled off under reduced pressure and the residue was purified bycolumn chromatography purification with a petroleum ether/ethyl acetategradient as eluent. 28.5 g (97.3 mmol) of ethyl2-bromo-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylate wereobtained. This was dissolved in 300 ml of methanol and the solution wascooled to 0° C. Then 300 ml (2N in water, 600 mmol) of sodium hydroxidewere added and the mixture was stirred at room temperature for 1 h. Themixture was concentrated on a rotary evaporator and neutralized byaddition of 1N HCl. Then it was extracted with ethyl acetate. Thesolvent was distilled off under reduced pressure and the target compoundwas obtained.

¹H NMR (300 MHz, D₆-DMSO) δ ppm: 1.09 (t, 3H), 2.86 (q, 2H), 3.64 (s,3H), 12.60 (s, 1H).

2-[2-Bromo-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To a solution of 9.02 g (34.0 mmol) of2-bromo-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylic acid inpyridine (50 ml) were added 5.00 g (26.1 mmol) ofN³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine and 5.01 g (26.1 mmol)of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI).The mixture was stirred at room temperature for three days.Subsequently, the solvent was distilled off under reduced pressure andthe residue was taken up in acetic acid (50 ml). The mixture was stirredat 100° C. for 6 h, cooled down to room temperature, slurried withwater, then filtered through a suction filter and dried, and hence thetarget compound was obtained.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.11 (t, 3H), 3.00 (q, 2H), 3.76 (s,3H), 4.15 (s, 3H), 8.19 (s, 1H), 9.15 (s, 1H).

2-[2-Bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

To a solution of 10.3 g (24.5 mmol) of2-[2-bromo-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinein dichloromethane (100 ml) were added 4.64 ml (122 mmol) of formic acidand 15.1 ml (172 mmol, 35% in water) of hydrogen peroxide. The mixturewas stirred at room temperature overnight and the reaction was ended byadding saturated sodium thiosulfate solution. The organic phase wasremoved, dried over sodium sulfate and filtered, and the target compoundwas obtained by removing the solvent under reduced pressure.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.27 (t, 3H), 3.74 (q, 2H), 3.92 (s,3H), 3.96 (s, 3H), 8.24 (s, 1H), 9.22 (s, 1H).

2-[2-(Cyclohex-1-en-1-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine

200 mg (0.44 mmol) of2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine,92.0 mg (0.44 mmol) of2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 15.3mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium were initiallycharged under a protective gas atmosphere. Then 3.5 ml of degasseddioxane and 1.8 ml of degassed aqueous sodium carbonate solution (1M)were added. The mixture was stirred at 92° C. overnight. After cooling,the solvent was distilled off under reduced pressure. The residue wastaken up in dichloromethane and washed with water. The organic phase wasremoved, dried over magnesium sulfate and filtered, and the solvent wasdistilled off under reduced pressure. The crude product was purified bycolumn chromatography purification with a cyclohexane/acetone gradientas eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.27 (t, 3H), 1.63-1.78 (m, 4H),2.25-2.29 (m, 2H), 2.38-2.42 (m, 2H), 3.73 (q, 2H), 3.91 (s, 3H), 3.95(s, 3H), 6.29-6.31 (m, 1H), 8.22 (s, 1H), 9.20 (s, 1H).

2-[2-Cyclohexyl-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-13)

143 mg (0.31 mmol) of2-[2-(cyclohex-1-en-1-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridinewere initially charged in 20 ml of methanol in an autoclave. Then 50 mg(0.04 mmol, 10%) of palladium on charcoal were added and the mixture wasstirred under a hydrogen atmosphere at 5 bar for 16 h. After thepressure had been equalized and the hydrogen atmosphere had beenremoved, the mixture was filtered through Celite and the solvent wasdistilled off under reduced pressure. The crude product was purified bycolumn chromatography purification with a cyclohexane/acetone gradientas eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm: 1.23-1.31 (t +m, 4H), 1.37-1.48 (m,2H), 1.52-1.62 (m, 2H), 1.69-1.73 (m, 1H), 1.78-1.83 (m, 2H), 1.93-1.96(m, 2H), 2.95-3.02 (m, 1H), 3.71 (q, 2H), 3.90 (s, 3H), 3.95 (s, 3H),8.20 (s, 1H), 9.19 (s, 1H).

3-Azido-5-(trifluoromethyl)pyridine-2-carbaldehyde

1 g (5.2 mmol) of 3-fluoro-5-(trifluoromethyl)pyridine-2-carbaldehydewere initially charged in 10 ml of dimethylformamide (DMF) and cooled to0° C. Then 0.34 g (5.2 mmol, dissolved in 10 ml of DMF) sodium azidewere added and the mixture was stirred at room temperature for 4 h. Thereaction was ended by adding 100 ml of water. Then extraction waseffected twice with 100 ml each time of ethyl acetate. The combinedorganic phases were washed with saturated sodium chloride solution,dried over sodium sulfate and filtered, and the solvent was removedunder reduced pressure. The crude product was used without furtherpurification.

tert-Butyl[2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]carbamate

To a solution of 800 mg (3.5 mmol) of2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-carboxylic acidin tert-butanol (20 ml) were added 1.3 g (4.72 mmol) of diphenylazidophosphate (DPPA) and 1.5 g (14.8 mmol) of triethylamine. Themixture was stirred at 80° C. overnight, cooled down and concentratedunder reduced pressure. Then 100 ml of water were added and the mixturewas extracted twice with 150 ml each time of ethyl acetate. The combinedorganic phases were washed with saturated sodium chloride solution,dried over sodium sulfate and filtered, and the solvent was removedunder reduced pressure. The crude product was purified by columnchromatography purification with an ethyl acetate/petroleum ethergradient (1:3→1:1) as eluent.

MS (ESI): 298 [(M+H)⁺]

2-Cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-amine

To a solution of 400 mg (1.3 mmol) of tert-butyl[2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]carbamate indioxane (10 ml) were added 10 ml of conc. hydrochloric acid. The mixturewas stirred at room temperature overnight and then concentrated todryness under reduced pressure. The crude product was used withoutfurther purification.

MS (ESI): 198 [(M+H)⁺]

2-[2-Cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine

To a solution of 130 mg (0.66 mmol) of2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazole-4-amine in toluene(10 ml) were added 280 mg (1.3 mmol) of3-azido-5-(trifluoromethyl)pyridine-2-carbaldehyde and 970 mg (3.4 mmol)of titanium isopropoxide. The mixture was stirred first at 50° C. for 5h and then at 100° C. for 1 h. After cooling to room temperature, 100 mlof water were added and the mixture was extracted twice with 100 ml eachtime of ethyl acetate. The combined organic phases were washed withsaturated sodium chloride solution, dried over sodium sulfate andfiltered, and the solvent was removed under reduced pressure. The crudeproduct was purified by column chromatography purification with an ethylacetate/petroleum ether gradient (1:2) as eluent.

MS (ESI): 368 [(M+H)⁺]

2-[2-Cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine(I-18)

A solution of 80 mg (0.22 mmol) of2-[2-cyclopropyl-5-(ethylsulfanyl)-1-methyl-1H-imidazol-4-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridinein dichloromethane (10 ml) was cooled to 0° C., and 173 mg (1.5 mmol,35% in water) of hydrogen peroxide and 50 mg (1.1 mmol) of formic acidwere added. The mixture was stirred at room temperature for 5 h, dilutedby adding 50 ml of dichloromethane, and then washed with saturatedsodium thiosulfate solution and saturated sodium hydrogencarbonatesolution. The organic phase was removed, dried over sodium sulfate andfiltered, and the solvent was removed under reduced pressure. The crudeproduct was purified by preparative HPLC with a water/acetonitrilegradient as eluent.

¹H NMR (400 MHz, D₆-DMSO) δ ppm=0.99-1.13 (m, 4H), 1.25 (t, 3H),2.23-2.30 (m, 1H), 3.64 (q, 2H), 3.99 (s, 3H), 8.78 (s, 1H), 8.90 (s,1H), 9.22 (s, 1H).

In analogy to the examples and according to the above-describedpreparation processes, it is possible to obtain the following compoundsof the formula (I):

Ex- ample Structure I-1

I-2

I-3

I-4

I-5

I-6

I-7

I-8

I-9

I-10

I-11

I-12

I-13

I-14

I-15

I-16

I-17

I-18

I-19

Note with regard to determination of mass detection: unless statedotherwise, the mass reported is the peak of the isotope pattern of the[M+H]⁺ ion with the highest intensity. The mass is detected by means ofa Shimadzu LCMS-2020.

NMR Data of Selected Examples

The NMR data of selected examples are listed either in conventional form(δ values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

In each case, the solvent in which the NMR spectrum was recorded isstated.

NMR Peak List Method

The 1H-NMR data of selected examples are noted in the form of 1H-NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets is listed. The pairs of δvalue-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore has the form:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

Calibration of the chemical shift of 1H NMR spectra is accomplishedusing tetramethylsilane and/or the chemical shift of the solvent,particularly in the case of spectra which are measured in DMSO.Therefore, the tetramethylsilane peak may but need not occur in NMR peaklists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional 1H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject-matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of 1H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of 1H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

-   Example I-1: ¹H-NMR (300.1 MHz, CDCl3): δ=8.5508 (2.0); 8.5470    (2.0); 8.2068 (2.2); 8.2017 (2.1); 7.1922 (6.7); 5.2290 (0.4);    4.0675 (16.0); 3.7541 (15.4); 2.9130 (1.2); 2.8884 (3.7); 2.8638    (3.8); 2.8393 (1.3); 1.8709 (0.6); 1.8606 (0.6); 1.8443 (1.0);    1.8327 (0.5); 1.8274 (0.7); 1.8169 (0.7); 1.8001 (0.4); 1.1284    (4.0); 1.1039 (8.0); 1.0793 (4.0); 1.0635 (1.6); 1.0555 (2.0);    1.0467 (2.6); 1.0392 (1.8); 1.0289 (1.1); 1.0116 (1.4); 1.0023    (1.9); 0.9946 (1.4); 0.9854 (1.2); 0.9754 (2.0); 0.9672 (1.2);    0.9496 (0.4); 0.0165 (0.5); 0.0116 (0.7); −0.0001 (12.3); −0.0123    (0.5); −0.0710 (5.9)-   Example I-2: ¹H-NMR (300.1 MHz, CDCl3): δ=8.6142 (2.0); 8.6103    (2.0); 8.1922 (2.0); 8.1872 (2.0); 7.1929 (4.1); 5.2280 (0.4);    3.9775 (15.2); 3.8905 (16.0); 3.7395 (1.0); 3.7148 (3.2); 3.6900    (3.3); 3.6653 (1.1); 3.4081 (3.5); 1.8877 (0.5); 1.8791 (0.6);    1.8709 (0.4); 1.8619 (1.1); 1.8507 (0.4); 1.8441 (0.6); 1.8355    (0.6); 1.8179 (0.3); 1.3742 (3.4); 1.3495 (7.2); 1.3247 (3.3);    1.1840 (0.4); 1.1151 (1.0); 1.1070 (2.5); 1.1010 (2.1); 1.0879    (3.8); 1.0668 (1.4); 1.0603 (2.2); 1.0516 (1.2); 1.0301 (0.3);    −0.0002 (5.6); −0.0718 (3.5)-   Example I-3: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=8.4328 (2.2); 8.4279    (2.2); 8.3150 (0.5); 8.2014 (2.2); 4.0143 (16.0); 3.9284 (1.1);    3.9077 (1.1); 3.7964 (14.2); 3.3682 (1.3); 3.3279 (129.7); 2.9887    (1.2); 2.9703 (3.9); 2.9519 (3.9); 2.9335 (1.3); 2.8902 (0.4);    2.6706 (2.0); 2.5059 (283.5); 2.5016 (360.4); 2.4974 (270.8); 2.3281    (2.0); 2.3238 (1.6); 2.1991 (0.3); 2.1874 (0.6); 2.1787 (0.7);    2.1665 (1.2); 2.1539 (0.7); 2.1469 (0.6); 2.1342 (0.3); 1.2329    (0.6); 1.1118 (4.1); 1.0934 (8.5); 1.0750 (4.0); 1.0481 (0.6);    1.0359 (1.4); 1.0297 (2.3); 1.0226 (1.4); 1.0151 (1.5); 1.0094    (2.1); 1.0028 (1.4); 0.9878 (1.3); 0.9804 (2.2); 0.9747 (2.9);    0.9685 (2.3); 0.9624 (1.8); 0.9496 (0.6); −0.0002 (56.0)-   Example I-4: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=8.6009 (2.9); 8.5966    (3.0); 8.4574 (3.0); 8.4536 (2.8); 8.3150 (0.4); 4.0311 (16.0);    3.8012 (14.7); 3.3214 (181.0); 2.9991 (1.2); 2.9804 (3.9); 2.9622    (4.0); 2.9436 (1.3); 2.6708 (2.0); 2.5020 (358.8); 2.3286 (2.1);    2.1919 (0.7); 2.1827 (0.8); 2.1703 (1.2); 2.1588 (0.8); 2.1505    (0.7); 2.1381 (0.4); 2.0859 (0.5); 1.2341 (0.6); 1.1183 (4.2);    1.0998 (8.6); 1.0816 (4.1); 1.0511 (0.6); 1.0330 (2.5); 1.0256    (1.4); 1.0191 (1.5); 1.0130 (2.2); 1.0066 (1.5); 0.9907 (1.2);    0.9828 (2.4); 0.9775 (2.9); 0.9712 (2.5); 0.9654 (1.9); 0.9517    (0.6); 0.1465 (0.4); 0.0000 (88.2); −0.1488 (0.4)-   Example I-5: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.0858 (4.0); 8.1341    (4.3); 4.1389 (16.0); 3.8029 (14.9); 3.3219 (123.8); 2.9817 (1.3);    2.9633 (4.0); 2.9449 (4.1); 2.9265 (1.3); 2.6709 (0.9); 2.5058    (131.1); 2.5017 (167.0); 2.4975 (123.0); 2.3283 (1.0); 2.1943 (0.6);    2.1863 (0.7); 2.1739 (1.1); 2.1618 (0.7); 2.1539 (0.6); 2.1413    (0.3); 1.1063 (4.3); 1.0880 (8.8); 1.0695 (4.1); 1.0540 (0.6);    1.0418 (1.4); 1.0355 (2.4); 1.0285 (1.4); 1.0214 (1.5); 1.0153    (2.1); 1.0085 (1.4); 0.9924 (1.2); 0.9849 (2.3); 0.9796 (2.8);    0.9729 (2.4); 0.9671 (1.8); 0.9543 (0.6); −0.0003 (25.9)-   Example I-6: ¹H-NMR (400.0MHz, d₆-DMSO); δ=8.5373 (2.0); 8.5315    (2.2); 8.2860 (2.0); 8.2831 (2.0); 5.7552 (0.6); 3.9793 (14.2);    3.7887 (16.0); 3.7374 (1.0); 3.7190 (3.3); 3.7005 (3.4); 3.6821    (1.0); 3.3197 (28.5); 2.6711 (0.4); 2.5241 (1.0); 2.5064 (49.7);    2.5020 (65.8); 2.4976 (47.9); 2.3290 (0.4); 2.2471 (0.6); 2.2386    (0.6); 2.2265 (1.1); 2.2144 (0.7); 2.2062 (0.6); 1.2780 (3.6);    1.2596 (7.9); 1.2411 (3.6); 1.1082 (0.5); 1.0960 (1.3); 1.0895    (2.1); 1.0820 (1.3); 1.0755 (1.2); 1.0691 (2.1); 1.0617 (0.9);    1.0526 (0.4); 1.0470 (0.3); 1.0316 (1.0); 1.0238 (2.1); 1.0184    (2.1); 1.0119 (2.3); 1.0057 (1.7); 0.9938 (0.5); 0.0075 (0.8);    −0.0002 (22.7); −0.0083 (1.0)-   Example I-7: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=8.8889 (2.5); 8.8843    (2.6); 8.6319 (2.4); 8.6275 (2.4); 5.7559 (6.7); 3.9884 (14.2);    3.8424 (16.0); 3.7470 (1.0); 3.7286 (3.3); 3.7101 (3.4); 3.6917    (1.0); 3.3233 (89.2); 2.6712 (0.4); 2.666 (0.3); 2.5244 (1.0);    2.5110 (26.2); 2.5067 (54.8); 2.5022 (73.5); 2.4977 (53.2); 2.4934    (26.0); 2.3289 (0.4); 2.2579 (0.6); 2.2495 (0.6); 2.2373 (1.1);    2.2252 (0.7); 2.2170 (0.6); 1.3976 (0.9); 1.2855 (3.6); 1.2671    (7.9); 1.2486 (3.5); 1.2355 (0.5); 1.1158 (0.5); 1.1037 (1.3);    1.0972 (2.1); 1.0895 (1.3); 1.0832 (1.2); 1.0769 (1.9); 1.0694    (0.9); 1.0581 (0.4); 1.0372 (1.1); 1.0294 (2.0); 1.0240 (2.0);    1.0175 (2.3); 1.0113 (1.7); 0.9993 (0.5); 0.0078 (0.6); −0.0002    (20.0); −0.0082 (0.9)-   Example I-8: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.0939 (2.8); 9.0885    (3.0); 8.9022 (2.6); 8.3141 (0.5); 5.7547 (0.9); 3.9937 (14.2);    3.9689 (0.4); 3.8786 (16.0); 3.7535 (0.9); 3.7352 (3.2); 3.7168    (3.3); 3.6984 (1.1); 3.3974 (0.4); 3.3304 (359.6); 3.3284 (350.0);    2.6753 (1.5); 2.6713 (1.9); 2.6667 (1.5); 2.5241 (4.9); 2.5065    (267.4); 2.5021 (349.9); 2.4977 (254.8); 2.3332 (1.5); 2.3288 (2.0);    2.3244 (1.5); 2.2637 (0.6); 2.2560 (0.6); 2.2439 (1.2); 2.2319    (0.7); 2.2229 (0.6); 2.2114 (0.4); 1.2867 (3.5); 1.2683 (7.9);    1.2500 (3.5); 1.1199 (0.6); 1.1082 (1.2); 1.1015 (2.0); 1.0942    (1.3); 1.0877 (1.2); 1.0816 (1.9); 1.0742 (0.9); 1.0627 (0.4);    1.0416 (1.1); 1.0337 (2.1); 1.0284 (2.0); 1.0220 (2.3); 1.0158    (1.8); 0.1458 (0.4); 0.0079 (3.5); −0.0002 (106.0); −0.0083 (4.5);    −0.1498 (0.4)-   Example I-9: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.1784 (3.8); 8.1965    (4.0); 5.7561 (3.7); 3.9829 (14.7); 3.9122 (16.0); 3.7131 (1.0);    3.6947 (3.4); 3.6762 (3.4); 3.6577 (1.0); 3.3254 (49.6); 2.5249    (0.5); 2.5114 (12.9); 2.5070 (27.1); 2.5025 (36.4); 2.4981 (26.3);    2.4937 (12.8); 2.2532 (0.6); 2.2449 (0.7); 2.2326 (1.1); 2.2205    (0.7); 2.2124 (0.6); 2.0864 (2.3); 1.3973 (1.7); 1.2719 (3.6);    1.2535 (8.1); 1.2350 (3.6); 1.1119 (0.5); 1.0999 (1.2); 1.0934    (2.1); 1.0856 (1.2); 1.0793 (1.2); 1.0728 (2.0); 1.0653 (0.9);    1.0575 (0.4); 1.0364 (1.0); 1.0285 (2.0); 1.0231 (2.0); 1.0165    (2.3); 1.0103 (1.7); 0.9982 (0.5); 0.0079 (0.6); −0.0002 (17.6);    −0.0083 (0.7)-   Example I-10: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.2269 (0.5); 9.1820    (3.9); 8.2490 (0.5); 8.1990 (4.1); 5.7580 (6.0); 4.5075 (0.7);    4.4897 (2.4); 4.4718 (2.4); 4.4541 (0.7); 4.3550 (0.6); 4.0057    (0.6); 3.9916 (0.6); 3.9821 (1.8); 3.9262 (16.0); 3.8175 (0.4);    3.7989 (0.4); 3.7653 (1.0); 3.7468 (3.4); 3.7283 (3.4); 3.7100    (1.0); 3.3233 (12.5); 2.5250 (0.5); 2.5112 (13.4); 2.5071 (27.0);    2.5028 (35.5); 2.4983 (25.4); 2.2781 (0.6); 2.2700 (0.6); 2.2575    (1.1); 2.2455 (0.6); 2.2375 (0.6); 1.4719 (2.6); 1.4542 (6.1);    1.4439 (1.1); 1.4365 (2.7); 1.4266 (1.1); 1.4089 (0.4); 1.3021    (0.5); 1.2987 (0.6); 1.2897 (0.5); 1.2799 (1.3); 1.2743 (3.7);    1.2558 (8.0); 1.2374 (3.7); 1.1340 (0.5); 1.1216 (1.2); 1.1152    (2.1); 1.1077 (1.2); 1.1008 (1.4); 1.0951 (1.9); 1.0875 (1.0);    1.0747 (0.4); 1.0653 (1.0); 1.0576 (2.3); 1.0523 (2.1); 1.0459    (2.2); 1.0396 (1.6); 1.0275 (0.5); −0.0002 (0.7)-   Example I-11: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.1739 (4.2); 8.1837    (4.4); 5.3190 (0.3); 5.3014 (0.9); 5.2839 (1.3); 5.2662 (1.0);    5.2492 (0.4); 3.8730 (16.0); 3.6436 (1.0); 3.6253 (3.4); 3.6067    (3.4);3.5884 (1.0); 3.3220 (67.8); 2.6705 (0.7); 2.5057 (90.9);    2.5014 (117.8); 2.4971 (85.1); 2.3575 (0.6); 2.3518 (0.7); 2.3387    (1.3); 2.3319 (1.1); 2.3273 (1.2); 1.7008 (13.4); 1.6832 (13.3);    1.3973 (1.1); 1.2796 (3.6); 1.2612 (8.0); 1.2428 (3.6)l 1.1254    (2.6); 1.1051 (4.1); 1.1013 (4.0); 1.0930 (2.7); 1.0887 (2.9);    −0.0003 (0.7)-   Example I-12: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=8.6935 (2.8); 8.6888    (3.0); 8.5473 (2.8); 8.5427 (2.7); 5.782 (9.7); 4.004 (0.9); 3.9889    (14.1); 3.9296 (0.4); 3.8864 (0.7); 3.8484 (0.4); 3.8078 (16.0);    3.7447 (1.2); 3.7263 (3.5); 3.7078 (3.5); 3.6894 (1.1); 3.3278    (6.4); 2.5105 (8.6); 2.5061 (11.5); 2.5017 (8.4); 2.2539 (0.6);    2.2457 (0.7); 2.233 (1.2); 2.2213 (0.7); 2.2131 (0.6); 1.3957 (2.3);    1.2868 (3.8); 1.2684 (8.0); 1.2498 (3.6); 1.1128 (0.5); 1.1009    (1.4); 1.0944 (2.2); 1.0867 (1.4); 1.0803 (1.3); 1.0739 (2.1);    1.0665 (1.0); 1.0580 (0.4); 1.0525 (0.3); 1.0375 (1.1); 1.0296    (2.2); 1.0243 (2.2); 1.0177 (2.4); 1.0114 (1.8); 0.994 (0.5); 00.76    (0.5); −0.0002 (14.7); −0.0082 (0.7)-   Example I-13: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.1866 (4.1); 8.1997    (4.4); 3.9497 (16.0); 3.9042 (14.6); 3.7334 (1.0); 3.7149 (3.4);    3.6964 (3.4); 3.6781 (1.1); 3.3199 (45.0); 3.0125 (0.5); 3.0045    (0.3); 2.9933 (0.6); 2.9845 (1.0); 2.9763 (0.6); 2.945 (0.3); 2.9559    (0.5); 2.6752 (0.6); 2.6710 (0.8); 2.666 (0.6); 2.5239 (1.9); 2.5063    (106.0); 2.5019 (143.4); 2.4975 (106.4); 2.331 (0.7); 2.3286 (0.9);    2.3241 (0.7); 1.9578 (1.2); 1.9272 (1.4); 1.8217 (1.2); 1.7892    (1.4); 1.7260 (0.6); 1.6942 (0.7); 1.6196 (0.5); 1.6116 (0.5);    1.5869 (1.3); 1.5510 (1.4); 1.5261 (0.6); 1.5197 (0.6); 1.4752    (0.6); 1.4429 (1.3); 1.4110 (1.5); 1.3982 (12.4); 1.3799 (0.7);    1.3034 (0.5); 1.2689 (4.3); 1.2504 (8.6); 1.2319 (4.1); 1.2107    (0.4); 0.0081 (0.4); 0.0001 (12.5)-   Example I-14: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.2002 (0.4); 9.1870    (4.0); 8.2166 (0.4); 8.2002 (4.3); 3.9504 (16.0); 3.9009 (14.1);    3.7241 (1.0); 3.7057 (3.3); 3.6871 (3.4); 3.6687 (1.0); 3.3220    (12.6); 2.9290 (0.3); 2.9159 (0.6); 2.9039 (0.7); 2.8903 (0.6);    2.8784 (0.4); 2.5251 (0.6); 2.5114 (13.7); 2.5073 (28.8); 2.5028    (38.6); 2.4983 (28.3); 2.4942 (14.1); 2.0866 (0.9); 1.7924 (1.7);    1.7823 (2.1); 1.7681 (2.4); 1.7595 (1.9); 1.7372 (0.7); 1.7287    (0.9); 1.4974 (1.2); 1.4661 (1.9); 1.4106 (1.0); 1.3974 (3.6);    1.3804 (1.1); 1.3679 (1.1); 1.3493 (0.5); 1.3354 (0.4); 1.2656    (3.7); 1.2472 (8.0); 1.2287 (3.5); 0.9867 (2.0); 0.9562 (10.4);    0.9428 (11.5); 0.0078 (1.2); −0.0002 (37.0); −0.0084 (1.7)-   Example I-15: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=9.1971 (1.7); 9.1871    (1.2); 8.3148 (0.6); 8.2075 (1.8); 8.2018 (1.3); 3.9878 (6.8);    3.9428 (4.9); 3.9216 (4.3); 3.8932 (6.1); 3.8040 (0.4); 3.7860    (1.4); 3.7675 (1.4); 3.7489 (0.4); 3.7115 (1.0); 3.6928 (1.0);    3.4178 (0.4); 3.4061 (0.5); 3.3186 (181.5); 2.6796 (1.0); 2.6749    (1.9); 2.6704 (2.8); 2.6659 (2.1); 2.5237 (9.6); 2.5189 (14.7);    2.5103 (172.2); 2.5058 (362.1); 2.5013 (487.1); 2.4967 (350.9);    2.4923 (170.5); 2.3371 (1.0); 2.3326 (2.1); 2.3280 (2.8); 2.3235    (2.1); 2.0857 (0.9); 2.0413 (0.7); 1.9977 (0.7); 1.9547 (0.7);    1.9221 (0.5); 1.8910 (0.4); 1.8656 (0.4); 1.8343 (0.4); 1.7600    (0.5); 1.7526 (0.5); 1.7295 (0.5); 1.6936 (0.4); 1.6544 (0.4);    1.5091 (0.4); 1.4781 (0.4); 1.3980 (16.0); 1.300 (1.5); 1.2815    (3.5); 1.2680 (1.4); 1.2630 (1.7); 1.2497 (2.5); 1.2313 (1.1);    0.1459 (1.8); 0.079 (15.6); −0.0002 (441.7); −0.0085 (18.5); −0.1496    (1.8)-   Example I-16: ¹H-NMR (400 MHz, d₆-DMSO): δ=9.1883 (4.6); 8.2050    (4.4); 8.1970 (3.2); 5.7558 (14.8); 3.9755 (16.0); 3.9436 (11.4);    3.9044 (10.4); 3.8916 (14.5); 3.7532 (1.0); 3.7349 (3.4); 3.721    (1.1); 3.7164 (3.6); 3.7086 (2.7); 3.679 (1.3); 3.6901 (2.5); 3.6717    (0.7); 3.3249 (48.6); 3.1587 (0.5); 3.1498 (0.6); 3.1399 (0.8);    3.1296 (0.6); 3.1213 (0.5); 2.9232 (0.4); 2.9151 (0.6); 2.9064    (0.4); 2.8855 (0.4); 2.5256 (0.9); 2.5120 (19.1); 2.5077 (40.6);    2.5032 (55.6); 2.4987 (41.3); 2.4944 (20.9); 2.3301 (0.3); 1.9679    (0.8); 1.9381 (1.0); 1.9195 (0.4); 1.9091 (0.4); 1.8975 (0.6);    1.8862 (0.9); 1.8757 (0.8); 1.8647 (1.1); 1.8552 (1.0); 1.8442    (0.7); 1.8346 (0.6); 1.7898 (1.0); 1.7593 (2.2); 1.7409 (1.7);    1.7295 (1.2); 1.7173 (0.8); 1.7077 (0.8); 1.6971 (0.4); 1.6567    (0.6); 1.6482 (0.9); 1.6378 (0.7); 1.6250 (1.9); 1.6157 (2.2);    1.6046 (1.4); 1.5932 (1.9); 1.5840 (1.4); 1.5607 (1.4); 1.5515    (1.4); 1.5337 (0.8); 1.5187 (0.5); 1.4335 (0.3); 1.4268 (0.3);    1.4190 (0.4); 1.3972 (3.4); 1.2779 (3.7); 1.266 (3.2); 1.2596 (8.5);    1.2483 (6.3); 1.2411 (4.1); 1.2297 (2.7); 1.1697 (0.4); 1.1620    (0.4); 1.1374 (0.9); 1.0995 (0.8); 0.9614 (6.7); 0.9443 (6.5);    0.9287 (4.0); 0.9125 (3.8); 0.0079 (2.1); −0.0002 (63.1); −0.0085    (3.0)-   Example I-17: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=1.02-1.13 (m, 4H), 1.27    (t, 3H), 2.23-2.28 (m, 1H), 3.73 (q, 2H), 4.00 (s, 3H), 4.02 (s,    3H), 4.02 (s, 3H), 8.65 (s, 1H)-   Example I-18: ¹H-NMR (400.0 MHz, d₆-DMSO): δ=0.99-1.13 (m, 4H), 1.25    (t, 3H), 2.23-2.30 (m, 1H), 3.64 (q, 2H), 3.99 (s, 3H), 8.78 (s,    1H), 8.90 (s, 1H), 9.22 (s, 1H)-   Example I-19: ¹H-NRM (400.0 MHz, d₆-DMSO): δ=0.99-1.12 (m, 4H), 1.24    (t, 3H), 2.24-2.30 (m, 1H), 3.63 (q, 2H), 3.99 (s, 3H), 8.24 (s,    1H), 9.19 (s, 1H), 9.41 (s, 1H).

USE EXAMPLES

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

For the coating of the test tubes, 9 mg of active ingredient are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml glass tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm of active ingredient solution and internal surfacearea 44.7 cm², given homogeneous distribution, an area-based dose of 5μg/cm² is achieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the tubes are stood upright and the fleas are knocked to the base of thetube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-1, I-2

Rhipicephalus sanguineus—In Vitro Contact Test with Adult Brown DogTicks

For the coating of the test tubes, 9 mg of active ingredient are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μ1 of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml glass tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm of active ingredient solution and internal surfacearea 44.7 cm², given homogeneous distribution, an area-based dose of 5μg/cm² is achieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult dog ticks (Rhipicephalus sanguineus), sealed with a perforatedplastic lid and incubated in a horizontal position in darkness at roomtemperature and ambient humidity. After 48 h, efficacy is determined. Tothis end, the ticks are knocked to the base of the tube and incubated ona hotplate at 45-50° C. for a maximum 5 min. Ticks which remainmotionless at the base or move in such an uncoordinated manner that theycannot attempt to escape from the heat by climbing upward are consideredto be dead or moribund.

A substance shows good efficacy against Rhipicephalus sanguineus if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the ticks were dead or moribund. 0%efficacy means that no ticks were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-2

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active ingredient formulation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-2, I-7, I-8

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 ppm: I-1,I-11

Lucilia cuprina Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive ingredient formulation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that no larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-1, I-2, I-7, I-8, I-11

Musca domestica Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activeingredient formulation of the desired concentration are populated with10 adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm: I-1

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 100 ppm: I-2

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: I-1

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 ppm: I-2

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 20 ppm: I-7,I-8

Myzus persicae—Oral Test

Solvent: 100 parts by weight of acetone

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up to the desired concentration with water.

50 μl of the active ingredient formulationare transferred intomicrotitre plates and made up to a final volume of 200 μl with 150 μl ofIPL41 insect medium (33% +15% sugar). Subsequently, the plates aresealed with parafilm, which a mixed population of green peach aphids(Myzus persicae) within a second microtitre plate is able to punctureand imbibe the solution.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: I-1,I-2

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 4 ppm: I-1,I-2, I-6, I-8, I-9, I-10, I-11, I-12, I-13, I-15, I-17

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 4 ppm: I-16

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 0.8 ppm:I-2, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-17

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 0.8 ppm:I-15, I-16

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone Emulsifier: 1.5 parts by weightof dimethylformamide alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive ingredient formulation of the desired concentration.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-6, I-12

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:I-2, I-7, I-11, I-15, I-16, I-17

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone Emulsifier: 1.5 parts by weightof dimethylformamide alkylaryl poly glycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active ingredient formulation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-1, I-2, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-15, I-17

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight of acetone Emulsifier: 1.5 parts by weightof dimethylformamide alkylaryl poly glycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Leaf discs of maize (Zea mays) are sprayed with an active ingredientformulation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillar has beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha:I-10, I-12

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-2, I-6, I-7, I-8

Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone Emulsifier: 1.5 parts by weightof dimethylformamide alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-1

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:I-6, I-16

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 g/ha: I-2

The invention claimed is:
 1. A compound of formula (I)

in which R¹ is (C₁-C₆)alkyl, R² is (C₁-C₆)alkyl, R³ is optionally singly or multiply, identically or differently substituted (C₃-C₈)cycloalkyl, where optional substituents are (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, halogen or cyano, X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q18

R⁴ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl, or (C₂-C₆)alkynyl, R⁵ is hydrogen, C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl, or (C₁-C₆)haloalkylsulfonyl, R⁶ is hydrogen, and n is 0, 1 or
 2. 2. A compound of formula (I) according to claim 1 in which R¹ is (C₁-C₄)alkyl, R² is (C₁-C₄)alkyl, R³ is optionally singly or multiply, identically or differently substituted (C₃-C₆)cycloalkyl, where optional substituents are (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, halogen or cyano, X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q18, R⁴ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl, or (C₂-C₄)alkynyl, R⁵ is hydrogen, C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl, or (C₁-C₄)haloalkylsulfonyl, R⁶ is hydrogen, and n is 0, 1 or
 2. 3. A compound of formula (I) according to claim 1 in which R¹ is (C₁-C₄)alkyl, R² is (C₁-C₄)alkyl, R³ is optionally singly or multiply, identically or differently substituted (C₃-C₆)cycloalkyl, where optional substituents are (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, halogen or cyano, X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1, Q2, Q3, Q4, Q5, Q6, Q10, Q11, Q12, Q13, Q14, Q15, Q16, Q17 or Q18, R⁴ is hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, or (C₂-C₄)alkynyl, R⁵ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl, or (C₁-C₄)haloalkylsulfonyl, and n is 0, 1 or
 2. 4. A compound of formula (I) according to claim 1 in which R¹ is methyl, ethyl, n-propyl, or isopropyl, R² is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl, R³ is optionally singly or doubly, identically or differently substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where optional substituents in each case are methyl, ethyl, n-propyl, i-propyl, difluoromethyl, trifluoromethyl, X is Q1, Q2, Q3, Q13, Q14, or Q15, R⁴ is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl, R⁵ is fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl or trifluoromethylsulfinyl, R⁶ is hydrogen, cyano, methyl, trifluoromethyl, fluorine or chlorine, and n is 0, 1 or
 2. 5. A compound of formula (I) according to claim 1 in which R¹ is ethyl, R² is methyl, ethyl or isopropyl, R³ is cyclopropyl (unsubstituted) or optionally singly or doubly, identically or differently substituted cyclohexyl, where optional substituents are methyl or trifluoromethyl, X is Q2, Q3, Q13, Q14 or Q15, R⁴ is methyl, R⁵ is trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, R⁶ is hydrogen, n is 0 or
 2. 6. An agrochemical formulation comprising compound of formula (I) according to claim 1 and one or more extenders and/or surface-active substances.
 7. An agrochemical formulation according to claim 6, additionally comprising a further agrochemically active ingredient.
 8. A method of controlling one or more animal pests comprising allowing a compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.
 9. The compound of formula (I) according to claim 5, wherein X is Q2.
 10. The compound of formula (I) according to claim 5, wherein X is Q3.
 11. The compound of formula (I) according to claim 5, wherein X is Q13.
 12. The compound of formula (I) according to claim 5, wherein X is Q14.
 13. The compound of formula (I) according to claim 5, wherein X is Q15. 